Benzyl-6-O-acetyl-2,3,4,6-tri-O-benzyl-α-D-galactopyranosid | 53765-91-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl-6-O-acetyl-2,3,4,6-tri-O-benzyl-α-D-galactopyranosid
• CAS: 53765-91-6
• 化学式: C₃₆H₃₈O₇
• 分子量: 582.694
• InChiKey: YEELBAWKPSBSET-BVMCXEQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  Benzyl 2,3,4-tri-O-benzyl-α-D-galactopyranosid 、 [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-(diacetylamino)-6-methylsulfanyloxan-2-yl]methyl acetate 在 DMTST 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到benzyl N,N-diacetyl-2-amino-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  N,N-Diacetyl-Glucosamine and -Galactosamine Derivatives as Glycosyl Donors

  摘要：

  N-Acetyl-glucosamine and N-acetyl-galactosamine were converted into the O-acetyl protected 1-methylthio-derivatives 1A,B which were then transformed into N,N-diacetyl derivatives 2A and 2B, respectively. Activation of 2A,B with DMTST afforded good glycosyl donors for the generation of P-linkages: thus, reaction with accepters 3a,b gave oligosaccharides 4Aa and 4Ba in high and 4Ab and 4Bb in good yields. Mono-N-deacetylation could be performed with NaOMe/MeOH in quantitative yield, thus concluding a convenient procedure for the formation of beta-linked GlcNAc and GalNAc glycosides.

  DOI：

  10.1016/00404-0399(50)14068-